Iso-maleimycin, a Constitutional Isomer of Maleimycin, from Streptomyces sp. QL37

被引：2
|
作者：
Uiterweerd, Michiel T. [1 ]
Santiago, Isabel Nunez [2 ]
van der Heul, Helga [2 ]
van Wezel, Gilles P. [2 ]
Minnaard, Adriaan J. [1 ]
机构：
[1] Univ Groningen, Stratingh Inst Chem, Nijenborgh 7, NL-9747 AG Groningen, Netherlands
[2] Leiden Univ, Inst Biol, Sylviusweg 72, NL-2333 BE Leiden, Netherlands
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 2020卷 / 32期
关键词：
Maleimycin; Streptomyces sp; Actinomycetes; Antibiotics; GC-MS; NATURAL-PRODUCTS; BIOSYNTHESIS; SHOWDOMYCIN; NITROSPOREUSINES; ANTIBIOTICS; ALKALOIDS;
D O I：
10.1002/ejoc.202000767
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Iso-maleimycin, a previously unknown constitutional isomer of the antibiotic maleimycin, has been detected in an extract ofStreptomycessp. QL37. Chemical synthesis of both maleimycin (20 % yield over seven steps) andiso-maleimycin, (15 % yield over six steps) allowed access to reference materials for identification. Gas Chromatography coupled Mass Spectrometry (GC-MS) analysis demonstrated that of the two isomers, only iso-maleimycin was present in the extract. This finding supports our hypothesis thatiso-maleimycin is a biosynthetic intermediate of lugdunomycin.Iso-maleimycin displays low antibiotic activity, with a Minimum Inhibitory Concentration (MIC) value on bothE. coliandB. subtilisof 250 mu g/mL.
引用
收藏
页码：5145 / 5152
页数：8
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